Revisiting the Thermal Behavior and Infrared Absorbance Bands of Anhydrous and Hydrated DL-Tartaric Acid

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Abstract
In this work, we studied the thermal behavior and infrared fingerprint of anhydrous and hydrated DL-tartaric acid via conventional and modulated Differential Scanning Calorimetry (DSC), Thermogravimetry (TGA), Fourier Transform Infrared Spectroscopy (FTIR), nuclear magnetic resonance (NMR), pH measurements, and ab initio density functional theory (DFT) calculations. Six samples were examined in total (raw, recrystallized from D2O solution, freeze-dried, and three heated samples). The results reveal that both forms (anhydrous and hydrated) do not exhibit melting prior to decomposition. It is also shown that the so-called DL-tartaric acid does not exist in the solid state in pure form, but it contains water and a tartaric acid oligomer, which is produced through esterification. Alteration of the chemical structure (reflected through decomposition) is initiated at quite low temperatures and is more pronounced for the hydrated form. Up to 75 °C, decomposition proceeds through esterification, while at higher temperatures it seems to be reversed due to the increase in water and decrease in COOH groups emerging through anhydride formation. Either upon heating or at sub-zero temperatures during freeze-drying, the hydrated form decomposes, and although some water is removed, new water is produced due to esterification. The conclusions are also supported by DFT calculations.

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